Jill & My First Threesome (MFF) | 2016

This is part 5 of an ongoing tale of my time with Jill. Earlier parts can be found in the comments.

So Jill and I became boyfriend and girlfriend, and we "came out" to her group of friends. Surprisingly, Mary took it all rather well, but a few of the other friends were pretty angry and they wouldn't talk to her for while. (For the curious: eventually those wounds healed).

In the meantime, something switched in Jill and my relationship. We spent more time together, and had great fun with each other's company, but the frequency and adventurousness of our sex life took a real dip. After about a month of this, I was contemplating how to bring it up--after all, I was still satisfied with our sex life, and definitely our improved romantic life, but I didn't want this to become a downward trend, especially considering that expanding our sexual experience was the whole reason Jill and I got together. Anyway, before I could even broach the subject, Jill brought it up to me herself one night while we were watching TV at her place.

She grabbed the remote and turned the TV off in the middle of some show and before I could say anything she'd slithered on top of me (how did she move like that?) and was kissing me passionately as her hands roamed around the back of my neck. Not wanting to waste the opportunity, I kissed her back, but something wasn't working for her, and she grabbed my hands and pulled them to her ass, hard. Looking me dead in the eyes, she broke our kiss and said, "I need you to fuck me like you did that first time."

Well, that was it and I was off. I flipped her over on the couch so that I was on top and my hands were practically tearing at her clothes--not taking everything off, just enough. I pulled her jeans down to her ankles; she wasn't wearing any panties and she was so wet. She pushed my jeans and underwear down just far enough to get my cock out and I started to enter her. She was so tight! Even though she was soaking wet, the lack of foreplay meant it took a little longer than usual to push inside of her, but her nails scraped my back and she looked at me again with that fire in her eyes: "Just fuck me!"

I grabbed her ass with one hand, held her down on her neck with the other and slammed myself inside of her hard. She started convulsing immediately... she was the first woman I ever slept with who could have vaginal orgasms and they are amazing! I waited a little bit for her orgasm to die down and then I started fucking her hard, ramming her into the couch over and over again, thinking only of my pleasure until I started to get close. "Fill me up," she begged, knowing how much that dirty talk sets me off, "fill my cunt with your huge cock!" And just like that I slammed as deep into her as I could go and exploded.

Afterwards, both of us panting, she talked about how much she'd been needing to just "fuck" with me again, in addition to all the "love making" we'd been doing. I agreed and mentioned that I was worried we'd lost sight of trying to expand her sexual horizons. I asked her what were some things she still wanted to try, and she confessed she'd been thinking a lot about our time in the strip club and really wanted to be with a woman but was nervous. She'd had a pretty conservative upbringing and thinking of herself as even remotely bisexual was difficult for her.

I suggested that maybe I could be a presence in the room--not to have a threesome, but just to be there for emotional support if she needed it and I could leave if she wanted that as well, and she seemed really excited about the idea.

Now we spent the next couple of weeks excitedly researching who we wanted her first female experience to be, and then fucking with enthusiasm after talking about it. We did a lot of searching on the Internet and found some good candidates, but ultimately Jill was too nervous about meeting someone for the first time, and we settled on a friend of mine from college, Ashley.

Ashley was 25, bisexual, 5'3, skinny, short dirty blonde hair, green eyes, small but perky tits, and oozed sexuality. Ashley had also expressed to me on a few occasions recently just how hot she thought Jill was, and that she was really impressed with me for "landing" her. I'd had something of a crush on Ashley in college, but had been too chickenshit to ever try anything. Jill knew this, but Jill was definitely not the jealous type, and she found Ashley sexy, comforting, and basically she just had all the qualities Jill was looking for.

I approached Ashley about it while we were both drunk the next weekend at a mutual friend's birthday party, and she was extremely excited, even after I explained all the details, including that I would be there for support.

The big day arrived and we decided to do it at Jill's place (that way if she wanted to me leave, I could go home.) I brought wine, and before Ashley came over we drank a few glasses. Jill was visibly trembling as the buzzer rang, but she was also clearly excited (she kept telling me how aroused she was, and her nipples could've cut diamonds).

Ashley came up, and it began just like the three of us hanging out always was: a few glasses of wine, some jokes, etc. But then the innocent touching that we always did seemed to become a little less innocent, at least between Jill and Ashley. When we hit our first awkward pause, it was because Jill was clearly thinking about what we were here for, and that's when Ashley broke out her pipe and suggested we smoke some weed.

After passing around the pipe a few times, Jill toked and as she held the smoke in her lungs, Ashley came over to her and started kissing her full on with no buildup. The two of them broke the kiss and they both breathed out a puff of smoke, and Jill had turned bright red. But weed makes all three of us super horny, and it seemed to break down the last of Jill's barriers. She basically attacked Ashley and the two of them started making out. Meanwhile, my pants started to get uncomfortable.

Ashley suggested that they move to the bedroom, and I looked at Jill as if to see if she wanted me to stay. She smiled at me, and I followed along like a puppy dog.

The two of them climbed on to the bed and I sat in the armchair in the corner and watched them undress each other. Jill took great pains to kiss every inch of Ashley's flesh as it was revealed and Ashley definitely enjoyed the attention. I was getting the show of a lifetime, especially considering that I'd been waiting over 6 years to get a view of Ashley's body.

Finally Ashley pushed Jill away from her and said, "This is your first time, so let me show you how it's done." Ashley's tongue slid down the length of Jill's gorgeous body and then she went to work teasing Jill's pussy. Jill moaned and writhed, and I found out later (I couldn't see it from my position), that Ashley was tonguing Jill's asshole, something that she and I hadn't done yet but Jill was clearly enjoying. As Ashley went back to work on Jill's pussy, fingering her and licking her clit, Jill looked over at me and I could see the fire in her eyes again.

"You can play with it if you want to," she said, and I needed no further cue to pull my pants down and free my aching cock. I took advantage of the live porn show in front of me and started jerking off.

Jill came very shortly after that, clamping her legs around Ashley's face and screaming loudly. As Ashley pulled herself off of Jill's pussy she noticed me stroking my cock and smiled at me, then leaned over to Jill and whispered something. Jill whispered something back, and then Ashley said, "I just wanted to get permission to tell you, Sam: Goddamn! If I'd known you had that nice of a body in college..." And I swear to God, I almost came right then and there, but I held back. I also didn't know what to say so I just sat there awkwardly, cock in my hand, as Jill flipped Ashley over and said, "My turn!"

Jill went down on Ashley for a while as Ashley helped guide her, which was a lot sexier than it sounds. Hearing this sexy little strumpet tell my girlfriend to circle her clit more slowly... it was a lot of stimulation, but I continued to deny my own orgasm (I was hoping to fuck Jill when this was over).

Eventually, Jill climbed back up Ashley's body and apparently asked her quietly, "What can I do to make you cum?" to which Ashley apparently said, "Let me ride your cock." All I heard was the two of them whispering and then Jill laughing. Then she came over to me (I was afraid she was going to ask me to leave), leaned in to my ear and said, "Will you fuck her for me?"

I was kind of in shock, and I said, "Are you sure?," feeling afraid of ruining things with Jill but also ruining this opportunity to fuck Ashley. She seemed to think about it for a moment, and then said, "Absolutely. No question." Then she opened her dresser drawer and handed me a condom.

Ashley had come over to us at this point and took the condom from Jill, and rolled it on me herself. I looked over at Jill, who started to walk over to the bed. "I want to watch," she said, and she climbed up onto the bed and spread her legs, fingering herself.

Ashley climbed on top of me and slowly slid herself down my cock, whimpering as she went. My head was spinning, but I didn't have to do any work at all. Ashley just started slamming herself up and down the length of my cock, screaming as she went, and Jill was making noises herself as she frigged her pussy. I finally got into the game, grabbed Ashley's hips, and began driving myself up into her. It didn't take long; Ashley screamed that she was going to cum, and that was enough to finally set me off as I started spurting into the condom. Jill continued to finger herself as we calmed down and came shortly thereafter. Jill and Ashley kissed and then Ashley went home for the night. Jill and I fucked and talked and fucked some more, and this eventually led to us having our first MMF threesome and then opening up our relationship.